CN105944139A - Soybean protein isolate-based biomedical adhesive and preparation method thereof - Google Patents
Soybean protein isolate-based biomedical adhesive and preparation method thereof Download PDFInfo
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- CN105944139A CN105944139A CN201610520473.3A CN201610520473A CN105944139A CN 105944139 A CN105944139 A CN 105944139A CN 201610520473 A CN201610520473 A CN 201610520473A CN 105944139 A CN105944139 A CN 105944139A
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- soybean protein
- protein isolate
- dialdehyde
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- dopamine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/10—Polypeptides; Proteins
- A61L24/108—Specific proteins or polypeptides not covered by groups A61L24/102 - A61L24/106
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0015—Medicaments; Biocides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0042—Materials resorbable by the body
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/08—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs
Abstract
The invention relates to a soybean protein isolate-based biomedical adhesive and a preparation method thereof. The method comprises the following steps: firstly, dissolving soybean protein isolate into phosphate buffer; then, adding 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide; stirring for reacting for 30-60 minutes, and then adding dopamine; continuously stirring for reacting for 10-36 hours; lastly, performing dialysis, centrifugal separation and freeze drying to obtain dopamine-modified soybean protein isolate; during use, the following steps are adopted: dissolving the dopamine-modified soybean protein isolate into the phosphate buffer; then, adding a cross-linking agent and an anti-inflammation anti-bacterial agent; mixing uniformly, and smearing the mixture on a wound; dropwise adding an FeCl3 solution, so that the wound can be bonded firmly within 20-120s. The prepared biomedical adhesive has the characteristics of rapid response and long-acting bonding, can achieve a very good bonding effect in in-vivo and in-vitro wet environments, has high biocompatibility, is fully biodegradable in vivo, and can promote rapid healing of the wound.
Description
Technical field
The present invention relates to biology medical material technical field, good biocompatibility, fully biodegradable strong in particular to bonding force in a kind of moist environment in vivo and in vitro and soybean protein isolate base bio-medical binding agent easy to use and preparation method thereof.
Background technology
The theory of modern medicine is not only to realize the rehabilitation of patient's prestissimo on the basis of reducing patient's misery to greatest extent, and also is intended to its outward appearance and can ideally recover.Therefore, clinical demand be continuously increased the development having promoted adhesive of medical to study and adhering technique in clinical application.B.C. about 3000, ancient Egyptian employed the mixture of a kind of band adhesive of medical characteristic the earliest, and Greeks pulled oil, lead oxide and water with olive and prepare medical plaster shape mixture later.But, until recent decades adhesive of medical is just developed rapidly, provide the favourable weapon of hemostasis and tissue adhesion for surgical operation.At present, the most business-like bio-medical binding agent includes Fibrin Glue, albumin-glutaraldehyde binding agent and acrylic resin based binder etc..But, use Fibrin Glue may cause propagation and the anaphylaxis etc. of some Hematogenic infectious disease；During the binding agent that some small molecule aldehyde materials of use are cross-linking modified, owing to the free of aldehyde material and precipitation can cause cytotoxicity and calcification.Therefore, almost without the business-like tissue adhesive that can be widely applied in the moist environment of inside and outside on current market.
The health of oneself can be sticked to marine rock or bottom of ship by marine mussel firmly, this is because the L-DOPA (DOPA) contained in the sea-mussel mucin of mussel byssus gland secretion has Ultrastrength adhesive power in water environment.Document is reported, dopamine (the L-3 similar to DOPA structure, 4-dihydroxy phenylpropyl alcohol ammonia) also there is the ability of stuck object in moist environment, the catechol group being because in dopamine molecule structure of tracing it to its cause tightly can be adhered to each other by non-covalent interaction with material surface.Further study show that, the primary amino radical reactivity in dopamine molecule structure is bigger, it is possible to the carboxyl generation amidatioon with some macromolecular materials is anti-, therefore can give material by dopamine graft modification and also have excellent adhesion property in moist environment.
Comparatively speaking, the soybean protein isolate of plant source has advantage in the application of biomedical materials field.Soybean protein isolate not only have raw material sources extensive, cheap and easy to get, compared with high water resistance and biodegradable and catabolite the advantage to human non-toxic's evil effect, and be applied to bio-medical material and animal sources can be avoided to infect transmission of disease risk.Research finds, soybean protein isolate also has blood coagulation and promotes the function of tissue regeneration.Simultaneously, containing substantial amounts of amino, hydroxyl and carboxyl isoreactivity group in soybean protein isolate, therefore can be grafted more dopamine by amidation process and obtain dopamine-soybean protein isolate complex, then use metallic ion coordination complexation and cross-linking agent is long-acting, it is cross-linking modified to stablize, strengthen adhesion strength and the stability of binding agent.
Summary of the invention
In order to improve the biocompatibility of bio-medical binding agent, strengthening its bonding force in moist environment in vivo and in vitro, the present invention first passes through amidation process and is grafted to by dopamine molecule on soybean protein isolate molecule, then uses Fe3+The two-step method of ligand complex and the long-acting crosslinking of cross-linking agent prepares soybean protein isolate base bio-medical binding agent.
The invention provides a kind of soybean protein isolate base bio-medical binding agent, its preparation and application is as follows:
(1) 100 mass parts soybean protein isolates are dissolved in the phosphate buffer of pH=7.4 under the conditions of 40 ~ 80 DEG C, it is subsequently adding 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride and the N-hydroxy-succinamide of 10 ~ 20 mass parts of 20 ~ 30 mass parts, regulation pH value of reaction system is 4 ~ 7, the dopamine of 40 ~ 60 mass parts is added after stirring reaction 30 ~ 60min under the conditions of 20 ~ 50 DEG C, the pH value maintaining reaction system is 4 ~ 7, stirring reaction 10 ~ 36h is continued under the conditions of 20 ~ 50 DEG C, finally dialyse, lyophilization obtains the soybean protein isolate that dopamine is modified；
(2) when using, the soybean protein isolate that 100 mass parts dopamine are modified is dissolved in the phosphate buffer of pH=7.4, it is subsequently adding the antiinflammatory antibacterial of the cross-linking agent of 10 ~ 30 mass parts, 0.05 ~ 0.5 mass parts, coating after mix homogeneously at wound, dripping 5 ~ 20 mass parts concentration afterwards is the FeCl of 0.02 ~ 0.2M3Solution, gently pressing wound, in 20 ~ 120s, wound just can firmly be bonded together.
In above-mentioned preparation and application, cross-linking agent described in step (2) is genipin, procyanidin, tea polyphenols, dialdehyde starch, dialdehyde chitosan, dialdehyde guar gum, dialdehydeκAny one or a few mixture of-carrageenan, dialdehyde sodium alginate, dialdehyde carboxymethyl cellulose, dialdehyde xanthan gum, dialdehyde pulullan polysaccharide, dialdehyde cellulose, dialdehyde Rhizoma amorphophalli glucomannan and dialdehyde Weilan gum.
In above-mentioned preparation and application, antiinflammatory antibacterial described in step (2) is any one or a few mixture in tea polyphenols, tannic acid, meropenem, Xi Sitading, tobramycin, netilmicin, amikacin, levofloxacin hydrochloride, ciprofloxacin, moxifloxacin hydrochloride, norfloxacin, enoxacin, pefloxacin, Sparfloxacin, benzylphenol, gentamycin, quadracycline, amoxicillin.
The present invention, compared with existing bio-medical binding agent, has the advantage that
(1) raw material that the present invention selects is soybean protein isolate, its not only have raw material sources extensive, cheap and easy to get, compared with high water resistance and biodegradable and that catabolite is to human body nonhazardous effect feature, but also animal sources can be avoided to infect transmission of disease risk, promote blood coagulation and inducing tissue regeneration；
(2) present invention had both avoided the toxicity problem of little molecule aldehyde cross-linking agent with genipin and the cross-linking modified soybean protein isolate of dialdehyde polysaccharide, the binding agent of preparation, enhanced again stability and the bonding force of binding agent；
(3) the bio-medical binding agent that the present invention uses two-step method to prepare has quickly response and long-acting bonding feature, it is possible to reach good bonding effect in environment moistening in vivo and in vitro；
(4) the bio-medical binding agent that prepared by the present invention has good biocompatibility and a biodegradable, catabolite nonhazardous effect and being fully absorbed by human body；
(5) the bio-medical binding agent that prepared by the present invention is easy to use, organizes and be possible not only to promote wound healing inside and outside adherend, and the misery that second operation can be avoided to bring to patient, meet the theory of modern medicine.
Detailed description of the invention
4 embodiments of the present invention are given below, by embodiment, the present invention are specifically described.It is important to point out, embodiment is served only for that the present invention is described further, it is impossible to being interpreted as limiting the scope of the invention, the person skilled in the art in this field can make some nonessential improvement and adjustment according to present disclosure.
Embodiment
1
100 mass parts soybean protein isolates are dissolved in the phosphate buffer of pH=7.4 under the conditions of 60 DEG C, it is subsequently adding 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride and the N-hydroxy-succinamide of 10 mass parts of 25 mass parts, regulation pH value of reaction system is 5, the dopamine of 50 mass parts is added after stirring reaction 40min under the conditions of 25 DEG C, the pH value maintaining reaction system is 6, continuing stirring reaction 24h under the conditions of 30 DEG C, finally dialysis, lyophilization obtain the soybean protein isolate that dopamine is modified；During use, the soybean protein isolate that 100 mass parts dopamine are modified is dissolved in the phosphate buffer of pH=7.4, it is subsequently adding the genipin of 15 mass parts, the quadracycline of 0.15 mass parts and amoxicillin, coating after mix homogeneously at wound, dripping 15 mass parts concentration afterwards is the FeCl of 0.1M3Solution, gently pressing wound, in 90s, wound just can firmly be bonded together.
Embodiment
2
100 mass parts soybean protein isolates are dissolved in the phosphate buffer of pH=7.4 under the conditions of 70 DEG C, it is subsequently adding 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride and the N-hydroxy-succinamide of 15 mass parts of 20 mass parts, regulation pH value of reaction system is 4, the dopamine of 40 mass parts is added after stirring reaction 60min under the conditions of 30 DEG C, the pH value maintaining reaction system is 6, continuing stirring reaction 18h under the conditions of 35 DEG C, finally dialysis, lyophilization obtain the soybean protein isolate that dopamine is modified；During use, the soybean protein isolate that 100 mass parts dopamine are modified is dissolved in the phosphate buffer of pH=7.4, it is subsequently adding the dialdehyde xanthan gum of 30 mass parts, the gentamycin of 0.05 mass parts, coating after mix homogeneously at wound, dripping 15 mass parts concentration afterwards is the FeCl of 0.15M3Solution, gently pressing wound, in 40s, wound just can firmly be bonded together.
Embodiment
3
100 mass parts soybean protein isolates are dissolved in the phosphate buffer of pH=7.4 under the conditions of 50 DEG C, it is subsequently adding 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride and the N-hydroxy-succinamide of 15 mass parts of 30 mass parts, regulation pH value of reaction system is 7, the dopamine of 60 mass parts is added after stirring reaction 40min under the conditions of 40 DEG C, the pH value maintaining reaction system is 5, continuing stirring reaction 30h under the conditions of 30 DEG C, finally dialysis, lyophilization obtain the soybean protein isolate that dopamine is modified；During use, the soybean protein isolate that 100 mass parts dopamine are modified is dissolved in the phosphate buffer of pH=7.4, it is subsequently adding dialdehyde pulullan polysaccharide and tea polyphenols, the levofloxacin hydrochloride of 0.2 mass parts of 25 mass parts, coating after mix homogeneously at wound, dripping 20 mass parts concentration afterwards is the FeCl of 0.08M3Solution, gently pressing wound, in 30s, wound just can firmly be bonded together.
Embodiment
4
100 mass parts soybean protein isolates are dissolved in the phosphate buffer of pH=7.4 under the conditions of 65 DEG C, it is subsequently adding 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride and the N-hydroxy-succinamide of 14 mass parts of 28 mass parts, regulation pH value of reaction system is 5, the dopamine of 49 mass parts is added after stirring reaction 55min under the conditions of 35 DEG C, the pH value maintaining reaction system is 7, continuing stirring reaction 36h under the conditions of 25 DEG C, finally dialysis, lyophilization obtain the soybean protein isolate that dopamine is modified；During use, the soybean protein isolate that 100 mass parts dopamine are modified is dissolved in the phosphate buffer of pH=7.4, it is subsequently adding the dialdehyde carboxymethyl cellulose of 28 mass parts, the tannic acid of 0.3 mass parts and norfloxacin, coating after mix homogeneously at wound, dripping 16 mass parts concentration afterwards is the FeCl of 0.18M3Solution, gently pressing wound, in 70s, wound just can firmly be bonded together.
Claims (3)
1. a soybean protein isolate base bio-medical binding agent, it is characterised in that with the modified soybean protein isolate of dopamine as base material, use Fe3+The two-step method of ligand complex and the long-acting crosslinking of cross-linking agent prepares soybean protein isolate base bio-medical binding agent, and its concrete preparation method is as follows:
(1) 100 mass parts soybean protein isolates are dissolved in the phosphate buffer of pH=7.4 under the conditions of 40 ~ 80 DEG C, it is subsequently adding 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride and the N-hydroxy-succinamide of 10 ~ 20 mass parts of 20 ~ 30 mass parts, regulation pH value of reaction system is 4 ~ 7, the dopamine of 40 ~ 60 mass parts is added after stirring reaction 30 ~ 60min under the conditions of 20 ~ 50 DEG C, the pH value maintaining reaction system is 4 ~ 7, stirring reaction 10 ~ 36h is continued under the conditions of 20 ~ 50 DEG C, finally dialyse, lyophilization obtains the soybean protein isolate that dopamine is modified；
(2) when using, the soybean protein isolate that 100 mass parts dopamine are modified is dissolved in the phosphate buffer of pH=7.4, it is subsequently adding the antiinflammatory antibacterial of the cross-linking agent of 10 ~ 30 mass parts, 0.05 ~ 0.5 mass parts, coating after mix homogeneously at wound, dripping 5 ~ 20 mass parts concentration afterwards is the FeCl of 0.02 ~ 0.2M3Solution, gently pressing wound, in 20 ~ 120s, wound just can firmly be bonded together.
Soybean protein isolate base bio-medical binding agent the most according to claim 1, it is characterised in that cross-linking agent described in step (2) is genipin, procyanidin, tea polyphenols, dialdehyde starch, dialdehyde chitosan, dialdehyde guar gum, dialdehydeκAny one or a few mixture of-carrageenan, dialdehyde sodium alginate, dialdehyde carboxymethyl cellulose, dialdehyde xanthan gum, dialdehyde pulullan polysaccharide, dialdehyde cellulose, dialdehyde Rhizoma amorphophalli glucomannan and dialdehyde Weilan gum.
Soybean protein isolate base bio-medical binding agent the most according to claim 1, it is characterised in that antiinflammatory antibacterial described in step (2) is any one or a few mixture in tea polyphenols, tannic acid, meropenem, Xi Sitading, tobramycin, netilmicin, amikacin, levofloxacin hydrochloride, ciprofloxacin, moxifloxacin hydrochloride, norfloxacin, enoxacin, pefloxacin, Sparfloxacin, benzylphenol, gentamycin, quadracycline and amoxicillin.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106512078A (en) * | 2016-10-07 | 2017-03-22 | 常州市鼎日环保科技有限公司 | Preparation method of medical adhesive |
| CN107011683A (en) * | 2017-04-17 | 2017-08-04 | 四川大学 | A kind of oxidation resistant edibility synthesized thin film of antibacterial and preparation method thereof |
| CN108187026A (en) * | 2018-03-16 | 2018-06-22 | 南京财经大学 | A kind of product that can promote wound healing |
| CN109135663A (en) * | 2018-06-12 | 2019-01-04 | 陕西科技大学 | Chitosan oligosaccharide is aoxidized for the purposes of modified polyurethane, aqueous polyurethane, adhesive and the preparation method of its preparation |
| CN110665050A (en) * | 2019-11-08 | 2020-01-10 | 江南大学 | Biological adhesive and preparation method thereof |
| CN111249519A (en) * | 2020-01-17 | 2020-06-09 | 浙江理工大学 | Skin wound adhesive repair material and preparation method and application thereof |
| CN111407920A (en) * | 2020-02-22 | 2020-07-14 | 武汉纺织大学 | Biological tissue hydrogel adhesive and preparation method thereof |
| CN111893334A (en) * | 2020-07-06 | 2020-11-06 | 江苏宏德特种部件股份有限公司 | High-toughness wear-resistant aluminum alloy and processing technology thereof |
| CN112121223A (en) * | 2020-10-16 | 2020-12-25 | 河南民兴生物科技股份有限公司 | Sericin medical dressing and production method thereof |
| CN112451735A (en) * | 2019-09-09 | 2021-03-09 | 天津大学 | Epsilon-polylysine-based mussel-like coordination adhesive and preparation method thereof |
| CN114634763A (en) * | 2022-03-21 | 2022-06-17 | 东莞市人民医院 | Cross-linked material with protein coating and preparation method thereof |
| CN115068664A (en) * | 2021-03-12 | 2022-09-20 | 浦项工科大学校产学协力团 | Bioadhesive compositions comprising mussel adhesive proteins and methods of making the same |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106512078A (en) * | 2016-10-07 | 2017-03-22 | 常州市鼎日环保科技有限公司 | Preparation method of medical adhesive |
| CN107011683A (en) * | 2017-04-17 | 2017-08-04 | 四川大学 | A kind of oxidation resistant edibility synthesized thin film of antibacterial and preparation method thereof |
| CN108187026A (en) * | 2018-03-16 | 2018-06-22 | 南京财经大学 | A kind of product that can promote wound healing |
| CN109135663A (en) * | 2018-06-12 | 2019-01-04 | 陕西科技大学 | Chitosan oligosaccharide is aoxidized for the purposes of modified polyurethane, aqueous polyurethane, adhesive and the preparation method of its preparation |
| CN112451735A (en) * | 2019-09-09 | 2021-03-09 | 天津大学 | Epsilon-polylysine-based mussel-like coordination adhesive and preparation method thereof |
| CN110665050A (en) * | 2019-11-08 | 2020-01-10 | 江南大学 | Biological adhesive and preparation method thereof |
| CN111249519A (en) * | 2020-01-17 | 2020-06-09 | 浙江理工大学 | Skin wound adhesive repair material and preparation method and application thereof |
| CN111407920A (en) * | 2020-02-22 | 2020-07-14 | 武汉纺织大学 | Biological tissue hydrogel adhesive and preparation method thereof |
| CN111893334A (en) * | 2020-07-06 | 2020-11-06 | 江苏宏德特种部件股份有限公司 | High-toughness wear-resistant aluminum alloy and processing technology thereof |
| CN112121223A (en) * | 2020-10-16 | 2020-12-25 | 河南民兴生物科技股份有限公司 | Sericin medical dressing and production method thereof |
| CN115068664A (en) * | 2021-03-12 | 2022-09-20 | 浦项工科大学校产学协力团 | Bioadhesive compositions comprising mussel adhesive proteins and methods of making the same |
| CN114634763A (en) * | 2022-03-21 | 2022-06-17 | 东莞市人民医院 | Cross-linked material with protein coating and preparation method thereof |
| CN114634763B (en) * | 2022-03-21 | 2022-11-11 | 东莞市人民医院 | Cross-linked material with protein coating and preparation method thereof |
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